Stack Exchange Uses HelloSign's API to Automate Stock Option Grants

A popular Q & A network for developers and programmers, Stack Exchange is renowned among computer engineers for collecting and featuring the very best answers to technical questions. So it only makes sense that their internal work systems follow suit.

Recouping Time and Bandwidth By Solving An Internal Paperwork Bottleneck

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4 times a year, Stack Exchange team members receive an email listing out their personalized stock option grants. With over 200 employees, that means hundreds of emails and paperwork flows sent round the Stack Exchange team.

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With each batch of grants requiring anywhere from 40 - 100 documents to be completed by employees, the quarterly task of organizing this paperwork came paired with a quarterly headache.

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The pain of tracking the paperwork trails was experienced most acutely by Stack Exchange’s CFO, Jack Sinclair, who orchestrated the process of sending, tracking, and collecting the paperwork. To alleviate this frustration (and to help regain employee bandwidth), Stack Exchange did what they do best:
They posed a technical question, “How can we effectively streamline the time, cost, and effort spent on tracking these docs?” and set about finding best solution.

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The answer came in the form of a quick HelloSign API integration to process and organize the paperwork flow.

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Using the HelloSign API to Reduce CFO Overhead

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Before integrating the HelloSign API, Jack and his team were responsible for creating, sending, and tracking each set of paperwork. Jack said that while the creation of each document was fairly straightforward (he used a mail merge to send out all the docs), tracking and following-up with the completed paperwork was challenging.

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“People would use different methods of signature (scanning, signing, and dropping off), so there was a lot of paperwork to organize before you could even check to see who was missing.”

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The time spent on the paperwork logistics was not only painful for Jack, the process of coordinating so many different steps resulted in increased paperwork errors and the resulting costs. Not to mention, extra employee energy was diverted to filling out paperwork rather than remaining focused on projects.

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To solve the issue of time spent paper chasing, Yaakov Ellis – one of Stack Exchange’s engineers – used the HelloSign API to streamline the process.

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Less Than a Week of Active Planning = Massive Time Saved and Reduced Paperwork Errors

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Now, Jack keeps a spreadsheet updated with all the key pieces of information necessary for each piece of stock option grants paperwork. But instead of sending out a mail merge email as he did before, he created a HelloSign template for the grants paperwork.

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The HelloSign API (integrated by Yaakov) runs through the spreadsheet and kicks out the correct paperwork to each employee who needs it. Employees use embedded signing to complete the paperwork and return all forms directly to Jack.

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Yaakov's work – including all dev work for the app, integration with the HelloSign API, testing and bug fixing – took a week. The active planning for the project took less than a week.

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The optimized paperwork workflow has allowed Jack to remove a frustrating (but necessary) admin component from his workload. And while time and revenue saving are often two big pros of streamlining paperwork, Jack was particularly excited to provide employees with an easy way to complete paperwork.

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“We do save a lot of time, hours upon hours, but the real benefit is the accuracy and completeness that was very difficult before.”

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The simple user interface makes it easy for employees to not only receive, but to quickly and accurately complete the paperwork. No need for printing and filling out physical paperwork; no need to worry about tracking down individual papers.

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What's Next?

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Since the first integration, Yaakov has extended the tool to send out two more documents to all US employees (over 100 people). Using the HelloSign API, he was able to further integrate these new paperwork flows into the existing tool in less than a day.

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They'll continue to organize and tweak their company workflows in the best way possible.